ChemInform Abstract: 1,2,3‐Trimethoxypropane and Glycerol Ethers as Bio‐Sourced Solvents from Glycerol. Synthesis by Solvent‐Free Phase‐Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations.

Abstract

Byline: Marc Sutter, Wissam Dayoub, Estelle Metay, Yann Raoul, Marc Lemaire Keywords: alkylation; Ci[pounds sterling] C coupling; glycerol; green chemistry; phase-transfer catalysis; transesterification Abstract 1,2,3-Trimethoxypropane (2), 1-alkoxy-2,3-dimethoxy-propanes, and 1-aryloxy-2,3-dimethoxypropanes were prepared in good yields and selectivity by solid-liquid phase-transfer catalysis in the presence of an inorganic base and an ammonium salt as the phase-transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150ag scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95%. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol and vegetable oil, organometallic reactions (Grignard- and Barbier-type reactions), carbon-carbon coupling reactions (Suzuki, Sonogashira, Heck), and in etherification reactions by dehydrogenative alkylation. The solvent showed interesting properties for the solubilization of polymers. Author Affiliation: Laboratoire de Catalyse, Synthese et Environnement (CASYEN), Groupe Lemaire, Institut de Chimie et Biochimie Moleculaires et Supramoleculaires (ICBMS), CNRS. UMR5246, Universite Lyon 1, Batiment Curien-CPE, 3[degrees] etage 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex (France), Fax: (+33)472431408 Sofiproteol, 11, rue de Monceau, CS 60003, 75378 Paris Cedex 08 (France) Laboratoire de Catalyse, Synthese et Environnement (CASYEN), Groupe Lemaire, Institut de Chimie et Biochimie Moleculaires et Supramoleculaires (ICBMS), CNRS. UMR5246, Universite Lyon 1, Batiment Curien-CPE, 3[degrees] etage 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex (France), Fax: (+33)472431408 Supporting information: Additional Supporting Information may be found in the online version of this article As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. CAPTION(S): miscellaneous_information